3-<(2-aminopropyl)thio>indole | 61021-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-<(2-aminopropyl)thio>indole
• 英文别名: S-(3-Indolyl)(2-amino-1-propyl)sulphide；3-(2-aminopropylthio)indole；1-(1H-indol-3-ylsulfanyl)propan-2-amine
• CAS: 61021-79-2
• 化学式: C₁₁H₁₄N₂S
• 分子量: 206.312
• InChiKey: HJLJWGUVEDDGJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  67.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-<(2-aminopropyl)thio>indole 、 5-ethoxy-1-methyl-3,4-dihydro-2H-pyrrolium, tetrafluoroborate 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 N-[1-(1H-indol-3-ylsulfanyl)propan-2-yl]-1-methylpyrrolidin-2-imine
  参考文献：
  名称：

  Cardiac-slowing amidines containing the 3-thioindole group. Potential antianginal agents

  摘要：

  A series of 3-thioindolamidines (and 3-indolamidines) related to mixidine (1) was studied for cardiac-slowing properties, following the discovery of activity for prototype thioindole 2. Structure-activity relationships were explored, leading to many potent antitachycardiac agents (6-9, 12, 13, 15-17, 20, 23, 24, 30, 34, 35, 45, and 47-49). Relative to 2, cardiac-slowing activity is enhanced by substitution of the indole nitrogen with small (C1-C3) saturated alkyl groups (6-9), unsaturated alkyl groups (12, 13, and 15-17), or a methoxyethyl group (20); replacement of the N-methyl group with alkyl (23) or phenyl groups (24); and extension of the ethylene bridge by two methylene units (34). Dethio (i.e., 3-indole) analogues of 2 with alkyl substitution on the indole nitrogen (47-49) have greater activity as well. Several potent compounds were also found to have minimal myocardial depression (6-9, 13, 45, and 47). Secondary pharmacological testing is reported for thioindoles 2, 6, 7, 9, and 28.

  DOI：

  10.1021/jm00356a021
• 作为产物：
  描述：

  1-((1H-吲哚-3-基)硫代)丙烷-2-酮 在 氢氧化钾 、 lithium aluminium tetrahydride 、 盐酸羟胺 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 20.0h， 生成 3-<(2-aminopropyl)thio>indole
  参考文献：
  名称：

  Nagarajan, K.; Arya, V. P.; Parthasarathy, T. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 8, p. 672 - 679

  摘要：

  DOI：

文献信息

• NAGARAJAN, K.;ARYA, V. P.;PARTHASARATHY, T. N.;SHENOY, S. J.;SHAH, R. K.;+, INDIAN J. CHEM., 1981, 20, N 8, 672-679
  作者：NAGARAJAN, K.、ARYA, V. P.、PARTHASARATHY, T. N.、SHENOY, S. J.、SHAH, R. K.、+

  DOI：——

  日期：——
• ZELESKO, M. J.;MCCOMSEY, D. F.;HAGEMAN, W. E.;NORTEY, S. O.;BAKER, C. A.;+, J. MED. CHEM., 1983, 26, N 2, 230-237
  作者：ZELESKO, M. J.、MCCOMSEY, D. F.、HAGEMAN, W. E.、NORTEY, S. O.、BAKER, C. A.、+

  DOI：——

  日期：——
• US4059583A
  申请人：——

  公开号：US4059583A

  公开（公告）日：1977-11-22
• Cardiac-slowing amidines containing the 3-thioindole group. Potential antianginal agents
  作者：Michael J. Zelesko、David F. McComsey、William E. Hageman、Samuel O. Nortey、Carol A. Baker、Bruce E. Maryanoff

  DOI：10.1021/jm00356a021

  日期：1983.2

  A series of 3-thioindolamidines (and 3-indolamidines) related to mixidine (1) was studied for cardiac-slowing properties, following the discovery of activity for prototype thioindole 2. Structure-activity relationships were explored, leading to many potent antitachycardiac agents (6-9, 12, 13, 15-17, 20, 23, 24, 30, 34, 35, 45, and 47-49). Relative to 2, cardiac-slowing activity is enhanced by substitution of the indole nitrogen with small (C1-C3) saturated alkyl groups (6-9), unsaturated alkyl groups (12, 13, and 15-17), or a methoxyethyl group (20); replacement of the N-methyl group with alkyl (23) or phenyl groups (24); and extension of the ethylene bridge by two methylene units (34). Dethio (i.e., 3-indole) analogues of 2 with alkyl substitution on the indole nitrogen (47-49) have greater activity as well. Several potent compounds were also found to have minimal myocardial depression (6-9, 13, 45, and 47). Secondary pharmacological testing is reported for thioindoles 2, 6, 7, 9, and 28.
• Nagarajan, K.; Arya, V. P.; Parthasarathy, T. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 8, p. 672 - 679
  作者：Nagarajan, K.、Arya, V. P.、Parthasarathy, T. N.、Shenoy, S. J.、Shah, R. K.、Kulkarni, Y. S.

  DOI：——

  日期：——